Triphenylphosphine → 4-[3-[4-(1-Imidazolyl)benzyloxy]phenyl]-4-methoxy-3,4,5,6-tetrahydro-2H-pyran

HRID 1291043

Reaktionsgleichung

Reaktionsgleichung von HRID 1291043
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.O[C:15]1[CH:16]=[C:17]([C:21]2([O:27][CH3:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:18]=[CH:19][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][O:11][C:19]3[CH:18]=[C:17]([C:21]4([O:27][CH3:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH:16]=[CH:15][CH:20]=3)=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2776486(4-(1H-Imidazol-1-yl)phenyl)methanolHCID 149858684-(3-hydroxyphenyl)-4-methoxy-3,4,5,6-tetrahydro-2H-pyran

Produkt 1

HCID 189201804-[3-[4-(1-Imidazolyl)benzyloxy]phenyl]-4-methoxy-3,4,5,6-tetrahydro-2H-pyranAusbeute 15,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 4-(1-imidazolyl)benzyl alcohol (Eur. J. Med. Chem., 1992, 27, 219) (0.87 g, 5.0 mmol), 4-(3-hydroxyphenyl)-4-methoxy-3,4,5,6-tetrahydro-2H-pyran (J. Med. Chem., 1992, 35, 2600) (1.03 g, 4.9 mmol) and triphenylphosphine (1.55 g, 5.9 mmol) in THF (30 ml) cooled to 0° C. was added dropwise a solution of diethyl azodicarboxylate (DEAD) (1.03 g, 12.0 mmol) in THF (10 ml) over 20 min under a nitrogen atmosphere. After completion of addition, the mixture was stirred at 0° C. for 30 min and allowed to warm to room temperature, and then volatiles were removed under reduced pressure. Chromatographic purification of the residue (SiO2, 230 g; gradient elution, 15% to 30% acetone in dichloromethane) provided 0.27 g of the title compound as a gum, which solidified on standing at room temperature. Fractions contaminated with triphenylphosphine oxide were combined, concentrated to dryness, solidified by triturating with diisopropyl ether and recrystallized from diisopropyl ether / ethyl acetate to provide 0.16 g of the title compound. Combined solids were further purified by recrystallization from diisopropyl ether / ethyl acetate afforded the title compound as tiny colorless needles (0.30 g, 17%).

Aufarbeitung

  1. additionAfter completion of addition
  2. temperatureto warm to room temperature
  3. customvolatiles were removed under reduced pressure
  4. customChromatographic purification of the residue (SiO2, 230 g; gradient elution, 15% to 30% acetone in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-3357a5d58def44f885c5748eaab9fd39
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753682

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